Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
  • C09B62/006—Azodyes
  • C09B62/008—Monoazo dyes
  • C09B62/0081—Monoazo dyes with coupling components containing an amino directing group

Definitions

• R stands for a hydrogen or halogen atoms, an alkyl or alkoxy group or an -NHacyl radical
• R for a hydrogen or halogen atom or an alkyl or alkoxy R for a hydrogen atoms or an alkyl or cycloalkyl radical
• X and Z independently of each other, for an atom chain completing a heterocyclic ring, which may be substituted and/or may bear a further ring system condensed on it;
• Y for a divalent organic radical which may be substituted and may be interrupted by an oxygen atom.
• Carboxylic acid and sulphonic acid groups are examples of water solubilizing groups from which the dyes of this invention are free.
• Chlorine and bromine atoms may be named as specially suitable halogen atoms.
• Th ealkyl and alkoxy groups in the dye molecule are preferably of low molecular weight, i.e. bearing 1, 2, 3, or 4 carbon atoms, and they may be substituted by chlorine or bromine atoms, alkoxy, cyanalkoxy, pyridyl, cyano, hydroxyl, acyl, phenyl or phenoxy radicals, of which the phenyl and phenoxy radicals may be further substituted.
• the cyclohexyl radical is a preferred cycloalkyl radical and like the alkyl groups it may be substituted.
• Non-water-soluble acyl radicals are, for example, those of formula R-P- and R'--Q-, where R represents a hydrocarbon radical, preferably a lower alkyl radical or a phenyl radical, which as defined above may be substituted and/or may contain hetero atoms, P represents -O-CO or SO R a hydrogen atom or R, Q is -CO, NR-CO- or NR"-4SO and R a hydrogen atom or R.
• radicals of formula are preferably radicals of five-membered heterocyclic compounds of aromatic character which may be substi tuted, for example, by halogen atoms, in particular chlotime or bromine atoms, nitro, cyano, alkyl, alkoxy, acyl or acylamino groups (all as defined above).
• Preferred members of these groups of radicals are thiazolyl, isothiazolyl, benzothiazolyl, thiophenyl, imidazolyl, l, 2, 4- or 1, 3, 4-thiadiazolyl, pyrazolyl, triazolyl or tetrazolyl radicals.
• a preferred radical of formula is the benzothiazolyl radical, which may be substituted, by, for example, halogen atoms, again preferably chlorine or bromine atoms, nitro or lower :alkoxy groups.
• halogen atoms again preferably chlorine or bromine atoms, nitro or lower :alkoxy groups.
• Further suitable radicals are thiazolinyl, thiazinyl and thiadiazolyl radicals.
• the preferred Y radicals are lower alkylene groups containing 1, 2, 3 or 4 carbon atoms, which may be substituted by, e.g., a hydroxyl or a lower alkylcarbonyloxy group, or a radical of formula Phenyl radicals, as substituents on the dye molecule, may be substituted, e.g., by chlorine or bromine atoms, nitro, thiocyano, cyano, lower alkyl or alkoxy groups, acyl or acylamino radicals (acyl as defined above).
• the dyes are produced by diazotizing an amine of formula and coupling the diazonium compound thus formed with a compound of formula
• D stands for a benzothiazolyl radical which may be substituted by a cyano, thiocyano, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, hydroxyalkylsulphonyl, cyanalkylsulphonyl or alkylaminosulphonyl group, a thiazolyl radical which may be substituted by a chlorine or bromine atom or an alkyl, cyano, nitro, N-morpholinoalkyl or alkylsulphonyl group, a 1, 2, 4-thiadiazolyl radical which may be substituted by an alkylsulphonyl group, a l, 3, 4-thiadiazoly1 radical which may be substituted by a chlorine or bromine atom or
• alkenyl and alkoxy represent lower radicals, i.e. containing 1, 2, 3 or 4 carbon atoms.
• the dyes of Formula IV are produced by diazotizing an amine of formula D-iNH
• the coupling reaction generally takes place in acid, if necessary bulfered medium with cooling, for example at 05 C.
• Sodium acetate is a suitable buffering agent.
• the dyes are worked up into dye preparations by the normal methods, e.g. by grinding in the presence of dispersing agents and/or fillers, and are subsequently vacuum or jet dried. After the addition of a suitable volume of water the dyeing preparations can be applied to the fibres by exhaustion dyeing, padding or printing processes at a long or short liquor to goods ratio.
• the dyes build up excellently on textile of fully synthetic or semi-synthetic hydrophobic organic substances of high molecular weight. They are Well suitable for dyeing and printing textiles of linear aromatic polyester fibres, cellulose acetate, cellulose triacetate and synthetic polyamide fibres. They are also dyeable on polyolefins, acrylonitrile copolymer fibres, and polyvinyl compounds.
• the known dyeing and printing methods are used, for example those described in French Pat. 1,445,371.
• the dyeings obtained have 'very good all-round fastness, being especially fast to thermofixation, sublimation, pleating, ozone, solvents, lubricants, dry heat, chlorine, rubbing and cross dyeing. They also have very good 'wet fastness properties, e.g. fastness to water, sea Water, perspiration and washing.
• the reserve of wool and the gas fume and light fastness properties merit special note.
• the dyes are extremely stable to the various forms of the permanent press finishing process.
• EXAMPLE 1 22 parts of 2-amino-6-methylsulphonylbeniothiazole are stirred into 300 parts of glacial acetic acid and diazotized with 8 parts of sodium nitrile in concentrated sulphuric acid. 3 parts of urea are added and the diazonium compound formed is coupled with 32 parts of 1-(2-benzothiazolylmercapto) 2 (N-ethyl-N 3" methylphenylamino)-ethane in glacial acetic acid. The resulting dye is filtered 01f, washed free of acid and dried. Applied from aqueous dispersion to polyester fibres, it gives dyeings of rubine shade which have excellent fastness properties, in particular fastness to thermofixation.
• EXAMPLE 3 7.6 parts of sodium nitrite are added to 100 parts of concentrated sulphuric acid and the temperature raised to 65. On cooling to 5 100 parts of a mixture of 15 parts of propionic acid and parts of glacial acetic-acid are added With stirring, the temperature being allowed to rise to 15, on which this temperature is held until the addition is complete. The mixture is then cooled at once to 05.
• EXAMPLE 4 9.75 parts of Z-amino-6-nitrobenzothiazole are suspended in 60 parts of water, 131 parts of concentrated sulphuric acid are added to the suspension, and it is then cooled to -5. A solution of 4.2 parts of sodium nitrite in 46.4 parts of concentrated sulphuric acid is added with cooling to 0", after which the mixture is stirred for 2 hours at the same temperature. The diazonium salt solution is allowed to drop slowly with stirring into 16 parts of 1- 2'-benzothiazolyl-mercapto -2 (N-ethyl-N-3"-methylphenylarnino)-ethane in a propionic acid-acetic acid mixture in the ratio 1:5 at 0. After 3 hours the mixture is poured into ice-water and the precipitated dye filtered off, washed with 'water and dried.
• EXAMPLE 5 14.5 parts of Z-amino-S-nitrothiazole are added in portions to 150 parts of concentrated sulphuric acid cooled to 0-5. To the resulting solution is added dropwise a solution of nitrothiazole sulphuric acid, prepared by slowly adding 7.6 parts of sodium nitrite to parts of concentrated sulphuric acid with stirring, allowing the temperature to rise to 65, cooling to 50 and stirring for 3 hours. The combined solution is coupled with 32 parts of 1- 2'-benzothiazolyl-mercapto -2-( N-ethyl-N-3 -methylphenylamin0)-ethane in glacial acetic acid. Aqueous sodium acetate solution is added slowly until the reaction is neutral to Congo paper. The dye settles out and is filtered off, washed until neutral and dried.
• Example 52 O C H l S NBC 0 CH CZHE wherein R is a member selected from the group consisting of hydrogen, chloro, bromo, 'alkyl, alkoxy and NHacyl;
• R is a member selected from the group consisting of hydrogen, chloro, bromo, alkyl and alkoxy;
• R is a member selected from the group consisting of hydrogen, alkyl, alkenyl and cyclohexyl;
• thiazolyl isothiazolyl, benzothiazolyl, thiophenyl, imidazolyl, -1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, pyrazolyl, triazolyl and tetrazolyl, any substituent on a substituted member being selected from the group consisting of chloro, bromo, nitro, cyano, thiocyano, alkyl, alkoxy, alkylthio, N-morpholinoalkyl, acyl and acylamino;
• Y is either a substituted or unsubstituted member selected from the group consisting of benzothiazolyl, thiazolinyl, thiazinyl and thiadiazinyl, any substituent on a substituted member being selected from the group consisting of chloro, bromo, nitro and alkoxy; and Y is either a substituted or unsubstituted member selected from the group consisting of lower alkylene and lower alkylene interrupted by an oxygen atom, any substituent of a substituted member being selected from the group consisting of hydroxy and alkylcarbonyloxy; each alkyl, each alkoxy and each cycloheXyl being either substituted or unsubstituted, any substituent thereon being a member selected from the group consisting of chloro, bromo, alkoxy, cyanalkoxy, pyridyl, cyano, hydroxy, acyl, phenyl and phenoxy; each phenyl substituent being either substituted or un
• each acyl being either RP-- or R'--Q-,
• R is a member selected from the group consisting of alkyl, alkenyl and phenyl;
• P is a member selected from the group consisting of O--CO and -SO R is a member selected from the group consisting of hydrogen and R;
• Q is a member selected from the group consisting of C, NR"--CO-- and --NR"SO and R" is a member selected from the group consisting of hydrogen and R; and each alkyl, each alkoxy and each alkenyl haying from 1 to 4 carbon atoms.
• D is a substituted or unsubstituted member selected from the group consisting of (a) benzothiazolyl, any substituent of which is selected from the group consisting of cyano, thiocyano, alkoxy, alkylthio, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, hydroxyalkylsulphonyl, cyanalkylsulphonyl and alkylaminosulphonyl; (b) thiazolyl, any substituent of which is selected from the group consisting of chloro, bromo, alkyl, cyano, nitro, N-morpholinoalkyl and alkylsulphonyl; (c) 1,2,4-thiadiazolyl, any substituent of which is selected from the group consisting of alkylthio and alkylsulphonyl; (d) 1,3,4-thiadiazolyl, any substituent of which is selected from the
• R is a member selected from the group consisting of hydrogen, chloro, bromo, alkyl, alkoxy, formylamino, alkylcarbonylamino, alkoxycarbonylamino, alkoxyalkylcarbonylamino, cyanalkylcarbonylamino, phenoxyalkylcarbonylamino, benzylcarbon-ylamino, benzoylamino, nitrobenzoylamino, chlorobenzoylamino, phenoxycarbonylamino, alkylsulphonylamino, phenylsulphonylamino and toluylsulphonylamino;
• R is a member selected from the group consisting of hydrogen and alkoxy
• R is a member selected from the group consisting of hydrogen, alkyl, cyanalkyl, chloralkyl, alkovyalkyl, cyanalkoxyalkyl, cyclohexyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, benzyl, phenoxyalkyl, pyridylethyl, aminocarbonylalkyl, alkylaminocarbonylalkyl, benzoylalkyl, alkenylsulphonylalkyl and toluylsulphonylalkyl;
• R is a member selected from the group consisting of alkylene, hydroxyalkylene, acetoxyalkylene and CH CH O:-CH CH R is a member selected from the group consisting of hydrogen; chloro and bromo;
• R is a member selected from the group consisting of hydrogen, nitro, ethoxy, chloro and bromo; and each alkyl, each alkoxy and each alkenyl having from 1 to 4 carbon atoms.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Coloring (AREA)
• Thiazole And Isothizaole Compounds (AREA)
• Plural Heterocyclic Compounds (AREA)

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• 1967
  • 1967-07-11 CH CH988267A patent/CH485814A/de not_active IP Right Cessation
• 1968
  • 1968-07-01 US US741338A patent/US3595852A/en not_active Expired - Lifetime
  • 1968-07-02 GB GB1228475D patent/GB1228475A/en not_active Expired
  • 1968-07-11 FR FR1574372D patent/FR1574372A/fr not_active Expired
  • 1968-07-11 BR BR200552/68A patent/BR6800552D0/pt unknown

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